Plot

Gilligan is forced to become the Howell's house-boy when the Skipper loses a bet to Mr. Howell in a turtle (actually a tortoise) race.

For entertainment, the Skipper (Alan Hale Jr) and Mr. Howell (Jim Backus) have been turtle-racing. After Howell's turtle wins for the 39th time in a row, the Skipper refuses to race again because he's lost everything he has in wagers to Howell, but Mr. Howell suggests that the Skipper wager Gilligan's service as a houseboy against Thurston's 60-foot yacht. The Skipper won't do it, but when he learns his turtle loves carrots, they plan to use carrots to beat Mr. Howell's turtle in a new race. However, when the Skipper makes the bet, Howell gets suspicious and asks Ginger (Tina Louise) to find out why he changed his mind on the bet. She goes to vamp Gilligan (Bob Denver) who spills the beans about the Skipper's turtle liking carrots. Howell then turns around and buys all the community vegetables from Mary Ann (Dawn Wells) for $16,000. Left without anything to tempt their turtle, they test a number of potential foodstuffs to tempt him, discovering he likes tree moss. Unfortunately, the Skipper loses again because Gilligan overfed their turtle on moss before the race. Mr. Howell takes Gilligan as a manservant which turns into a disaster because, as hard as he tries, Gilligan fouls up everything. The Skipper meanwhile is heartbroken without his "little buddy," but Gilligan convinces him to bet Mr. Howell again with his pocketknife as the wager. Howell agrees to the new race, but Mrs. Howell (Natalie Schafer) implores him to let the Skipper win. Meanwhile, Ginger lifts the Skipper's spirits by convincing him that the day of the race is his lucky day. That night, Mrs. Howell switches the turtles to favor the Skipper, then Mr. Howell switches the turtles for the same reason. When Gilligan sees this, he tells the Skipper what Mr. Howell did, but not wanting to win that way, he tells Gilligan to switch them back. When Gilligan tells Mr. Howell that the Skipper wants an honorable race, he has Gilligan switch them back. In the end, everyone has their original turtle back, and Mr. Howell is shocked to learn he has won and acquired Gilligan's pocketknife. Eager to get rid of Gilligan, he has the Skipper guess which of his hands has a pebble in it. The Skipper loses because neither of his hands has a pebble, but the Skipper gets Gilligan anyway because as Howell points out where Gilligan is concerned, the loser is the winner. He then walks away with damages to his clothes from when Gilligan did his laundry.